


Just the Way I'm Supposed to Be

by greendalecoolcat



Category: Community (TV)
Genre: F/M
Language: English
Status: Completed
Published: 2016-04-16
Updated: 2016-05-23
Packaged: 2018-06-02 16:24:06
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 11,609
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6573436
Author URL: https://archiveofourown.org/users/greendalecoolcat/pseuds/greendalecoolcat
Summary: <blockquote class="userstuff">
              <p>Single dad/Teacher AU</p><p>Jeff is a single dad to his four-year-old son. Annie is a preschool teacher.</p>
            </blockquote>





	1. He didn't get that from me

**Author's Note:**

> I'm not sure what this is, but I thought I'd give it a shot! Let's see how this thing turns out...

It was his son’s first day at his new preschool and Jeff was a little more than flustered. As a lawyer and single dad, he spent most of his time working while dedicating what little free time he had to his son, Matthew. Jeff knew it was a good school, but he feared that Matthew wouldn’t be able to handle a full school day after spending his summer days with his grandmother or Auntie Shirley.

“So, you ready for school today, bud?” Jeff asked from the front seat of the car. He was griping the steering wheel, knuckles white. He was even more nervous than his son. He just wanted to know that he would make it through the day without him.

“Yes,” Matthew was looking out the window, Spider-man backpack in hand. When his father told him he would be attending school in a strange, new place, he wasn’t too excited.

“You’re gonna love it,” Jeff tried to sound convincing, but who was he kidding? He never enjoyed school so why would his son? Maybe by some slim chance he would actually enjoy it.

When he pulled up to the preschool, both Jeff and Matthew let out a sigh. Jeff paused a moment before moved. _Hurry up, Winger. Now or never._ He got out of the car and went around to get his son out of his car seat. He gave Matthew a somewhat reassuring smile before they walked in the school together.

“Why can’t I go to Auntie Shirley’s instead?” Matthew asked when they got inside.

“Because Auntie Shirley has a business to run, buddy. And Elijah and Jordan have school today too.”

When they made it to the room, there was a whirlwind of kids running around playing with toys and screeching. One of the school teachers noticed the shell-shocked Jeff and Matthew and walked over to be of assistance.

“Hi, are you two new?” She smiled at Matthew and then up at Jeff.

Jeff was caught-off guard for a number of reasons. The first being the craziness of the children all around him. Second, he was now staring at a beautiful woman with the brightest blue eyes he had ever seen. She was wearing an adorable floral skirt and a yellow cardigan. But her radiant smile is what left him speechless.

When he didn’t respond, the woman tilted her head and suppressed a small laugh.

Jeff snapped out of it when he saw Matthew look up at him, “Oh! Uh, yeah. Jeff Winger,” he extended his hand for her to shake. After she took it, his hand dropped to his son’s shoulder, “And this is Matthew.”

The woman leant forward and extended her hand, “Hi, Matthew! I’m Ms. Edison! I’ll be your teacher this year.” Matthew shyly took Ms. Edison’s hand. “I love your backpack, that’s my friend’s favorite superhero,” she smiled.

Jeff chuckled at his son’s evident shyness. _He didn’t get that from me_ , he thought.

“So Matthew, you can go put your things in a cubby and then go off and play until we get started! We have an arts and crafts table, books to read, and a lot of toys lying around!”

Matthew gave his father a nervous look and it killed Jeff. He really needed this to work.

Jeff crouched down in front of his son, “That sounds like fun, right?” When that didn’t change Matthew’s expression he tried again, “Hey. You’re gonna have a good day, okay? Ms. Edison is really nice and you’re gonna learn a lot. And I’ll be right back here to pick you up this afternoon. I promise. Okay?”

Matthew nodded at his father.

Jeff kissed his son’s head before standing up. “Alright, go on,” he smiled.

He watched Matthew place his things inside of a cubby and then he went over to the arts and crafts table to draw a picture.

“He’ll be fine,” Ms. Edison smiled reassuringly at Jeff.

“I know. Thanks. He’s just been having a hard time lately, so I’m hoping this school works out for him.”

“Well he’s in good hands.”

“Yes, thank you, I appreciate it, Ms. Edison.” Jeff looked at his watch, “Crap. I have to get to work… If he needs anything…”

“We’ll give you a call,” she smiled, laughing slightly at his protectiveness.

Jeff let out breath of laughter at his ridiculousness, “Thanks.” He smiled at Ms. Edison one last time before he walked out the door.

 

* * *

 

Jeff’s day at work went on as normal, he knew Matthew was in good hands thanks to Ms. Edison. He was able to worry less about his son and actually focus on his work. Well, he tried. He really did. But he couldn’t get the image of bright blue eyes out of his mind. And a cute yellow sweater buttoned just enough to reveal a smidge of cleavage. Chestnut hair falling in soft waves. And the smile. That smile. Wait. He needed to stop. She is his son’s _teacher_.

Jeff snapped out of his day dream to realize it was 3:00 and time to pick up Matthew from his first day. Being a single dad was really tough, but he wouldn’t trade it for the world. Sure, Kristen left them cut and dry, she didn’t want the life she was given. She hadn’t fallen in love with Matthew, how could she have? How could you leave your own son and truly love him?

And it was no question that she never really loved Jeff. He was her trial-and-error relationship. She thought she wanted that life, but she bolted when she got bored.

Maybe Jeff never loved her either. Maybe he was trying to prove his own father wrong. Prove that he could stay in a lasting relationship and be a good dad.

At least he got the good dad part right.

But after Kristen left, it was just Jeff and Matthew. With the occasional help from his mother and his good friend Shirley, Jeff was raising his son on his own. He moved them into an apartment, just big enough for the two. And they were doing fine, but Jeff could see that Matthew was confused about his mom. He only heard from her every two weeks with a phone call from God knows where. It’s been tough on him.

So when Jeff arrived back at the preschool, he was relieved to find Matthew playing with a little blonde girl. He was so engrossed in their game that he didn’t even notice Jeff standing at the door.

Jeff was smiling at his son when someone stood beside him.

“Mr. Winger?”

Her beautiful eyes were looking up at him.

 _Snap out of it,_ “Uh, hi.” He looked down at her. “You can call me Jeff by the way,” he shot her a lopsided grin.

She beamed, “Well, _Jeff_. Matthew had a great day. He even made a friend,” she gestured to the little blonde girl. “Emily.”

“Yeah, I see that! You have no idea how relieved I am. He needs this,” Jeff looked back at his son. He loved seeing him happy.

In that moment, Matthew spotted his dad and ran to him, “Dad! Look what I made.” He handed him a bunch of drawings and crafts.

“Wow, look at all of this! Great job, buddy. Go get your stuff so we can head out,” he nodded towards the door.

Once Matthew was ready with his backpack and jacket, he walked back over to Jeff, “Can we get pizza, daddy?”

Jeff sighed, “Why not? I will succumb to the carbs, but only for you.” He roughed up his son’s sandy-blonde hair before turning back to his teacher, “Alright, say goodbye to Ms. Edison.”

Matthew did just that and began tugging at his dad’s hand.

“Bye, Matthew, I’ll see you tomorrow!”

When Matthew was no longer paying attention, Jeff spoke again, “Hey, uh. I really appreciate you looking out for him. I haven’t seen him this happy in a while. Thank you again, Ms. Edison.”

“It’s my pleasure,” she smiled at him. Before she walked away she whispered to him, “It’s Annie.”

Jeff held his breath as he watched her chestnut hair sway against her shoulders. _Get it together, Winger_.


	2. Some Sort of Energy

**Summary for the Chapter:**

> Family Day and flirtatious conversations.

**Notes for the Chapter:**

> This chapter takes place a few months into the school year.

Annie was in a good mood lately. She was having a great school year and her class was well behaved and adorable. It was her first time teaching, other than being an assistant like the previous few years. The past year had been filled with screw-ups, bad relationships, and a nightmare of a class.

Annie likes to think every child is capable of learning, but sometimes there is just no hope. And that was her class last year.

But this year was different. Things were great. And so were the people. They were really really really great—

“Good morning, Annie.” She turned around to see Jeff Winger giving her a charming smile with his hands on his son’s shoulders.

“Hi, Jeff! Good morning,” she gave him a sweet smile of her own before she looked to Matthew. “Good morning to you to, Matthew! Are you ready to learn today?”

Matthew nodded, still a bit shy. It was probably a trait he would always have.

“What’s on the agenda today, Ms. Edison?” Jeff asked, trying to engage his son.

“Today we’re learning about the solar system!” Annie’s eyes grew wide with excitement and she clasped her hands together.

“Wow! That sounds amazing!” Jeff tried to match her enthusiasm.

Matthew nodded his head once more, clearly wanting nothing more than to go join his friends at the arts and crafts table.

“Alright, go ahead.” Jeff laughed and squeezed his son’s shoulder, “I’ll see you later.”

“They grow up so fast,” Annie joked with him.

“Don’t remind me…”

“He really is doing great. He’s been enjoying the material and socializing. And he’s a sweetheart,” Annie bumped Jeff’s shoulder. _Where did that come from?_ She quickly snapped out of whatever compelled her to do that.

Jeff laughed, “I’m glad to hear it. Anyway, I should get to work. Have a good day, Annie.”

As he turned to leave, Annie blurted out, “Friday is Family Day!”

He looked at her quizzically.

“Oh uh, parents and guardians spend the day with their kids and we have a little party…” She smiled hopefully.

“I wouldn’t miss it,” he smiled.

As Jeff was walking out, Matthew’s friend Emily was walking in with her mother. She approached Annie and gave her a quick raise of the eyebrows.

“Hi Emily! Hi Britta,” she smiled at the blonde woman. Britta was another parent whom she’d gotten to know over these past few months.

“Holy Hot Dad, Batman! Who was that?”

“Britta!” She gasped.

“What?! It’s true…”

As much as Annie wanted to agree, fitted suit and attractive stubble and all, she rolled her eyes, “That was Jeff. He’s Matthew’s dad. Emily and Matthew are actually really great friends.”

“Are they now? I guess I’ll have to meet this _Jeff_.”

Annie’s face fell when she realized Britta seemed interested in more than _meeting_ him. “Oh well, he’s a single parent too, I mean I think so. No wedding ring. So I guess I can see if he’s available for you,” she shot Britta a half-hearted smile.

“Annie,” the blonde groaned. “I’m not _interested_ in him. I just want to meet the father of my kid’s friend. Who just so happens to be fairly attractive.”

“Oh…”

“Plus, I’m not about to mess up whatever it was that I walked in on,” she raised an eyebrow at Annie.

“What do you mean?!”

“You know what I mean. There was definitely some sort of energy between you two.”

Annie shook her head and began to walk away. “Goodbye, Britta,” she called over her shoulder.

 

* * *

 

Annie thought about what Britta had said all day. Was there some sort of energy between her and Jeff? She definitely found him attractive. And they did have a semi-flirtatious conversation every morning. She’s a single woman! What could she say?

But she really didn’t know much about the guy. She knew Matthew and she knew that Jeff was a lawyer, but she didn’t know much about their home life. Was there a woman in the picture? Maybe he had a girlfriend.

Jeff was a hard man to read.

Annie was humming while cooking dinner when her roommates walked through the door.

“Hey, Annie.”

“Hey Abed! Hi Troy!” She continued doing her task while she sparked a conversation, “Did you guys get any filming done today?”

“We tried, but Pierce was being difficult.” Troy shook his head and made his way over to his recliner.

“Pierce?” Annie asked, seeking clarification.

“One of the actors. Very temperamental,” Abed shook his head and sat in his respective recliner next to Troy.

“How was your day?” Troy called.

“It was good!” Annie smiled thinking about her successful introduction of the planets, “We learned about the solar system.”

Without skipping a beat, Abed spoke, “Are you seeing someone?”

Annie dropped the spoon she was holding, “What? Abed!”

Troy looked up with intrigue and interest.

“You’ve been humming lately. And making pancakes. And you haven’t gotten mad at Troy and I for spilling spaghetti sauce on the carpet.”

“That doesn’t mean I’m seeing someone, Abed! I’ve just…had a good couple of weeks!”

Abed looked at her curiously, “Okay.”

Annie just shook her head, “And don’t forget, you guys are coming to Family Day on Friday, right?”

“You know it,” Troy answered before exchanging his handshake with Abed.

It was quiet for a moment before Annie realized something Abed had said, “You spilled _WHAT_ on our carpet?!”

 

* * *

 

It was finally Friday and Annie was excited for the day. She got help from Troy and Abed and together they set up the classroom with cute decorations and a banner that read ‘Family Day’ in colorful puffy paint. Annie didn’t have the greatest family life growing up, so she was happy to celebrate with her two best friends and her wonderful preschool class.

A few parents began to trickle in with their kids when she spotted Jeff shuffle in with Matthew. He looked so handsome. Instead of his typical suit and tie, he was wearing a fitted navy blue button down, sleeves rolled up revealing his forearms. His hair was perfectly‒ _Oh, snap out of it, Edison_.

“Hi, Ms. Edison!” Matthew called up at her, Jeff trailing behind him.

Annie was surprised by Matthew’s level of enthusiasm; he was usually pretty timid, “Hi there! Are you excited for Family Day?”

He nodded and looked up at his dad, “Are you, daddy?”

“Absolutely!” Jeff picked up his son so they were at each other’s eye level, “I wouldn’t miss it.”

 _Oh my God he is so unbelievably cute._ Annie was looking adoringly at Jeff. In that same moment, Troy and Abed made their way over.

She snapped out of it when Abed and Troy were suddenly shaking hands with Jeff, “Hi, I’m Abed.” “Troy.”

“Abed, Troy.” Jeff nodded, Matthew still in his arms. “I’m Jeff. This is my son Matthew.”

“Oh, um!” Annie piped up when she realized what was happening. “These are my roommates!” She turned to look the pair, “Matthew is one of my students. Obviously. I mean, Jeff isn’t my student. This is a preschool…”

The guys, with the exception of Abed who was looking on curiously, chuckled at Annie’s rambling.

Trying to recover, she turned to Jeff’s son, “Matthew, my friend Troy is the one who loves Spider-Man just like you!”

After hearing that, Troy began animatedly talking about said superhero with Matthew, who was thoroughly enjoying it. Annie was watching Jeff when he met her eyes over the laughter of his son.

They held each other’s gaze for longer than probably necessary, but Annie didn’t care. His smile was magnetic; she couldn’t look away. She didn’t want to look away.

The moment was broken when Britta came over, Emily in hand. “Hey, Annie!”

Annie’s eyes parted from Jeff’s, “Hi, Britta. Emily!” She waved down to the little girl.

At this point, Jeff let Matthew back down on his feet so he could run off with his friend.

Jeff turned to look at Britta, arms crossed over his chest, “So you’re Emily’s mom. I guess you’re the reason why my son has been running around our apartment yelling ‘Don’t let the patriarchy win, Dad!’” He was holding back a smile, because let’s face it, that image was pretty freaking adorable.

Britta mirrored his position, “What can I say? Emily is a fast learner.”

Annie stifled a laugh, “O-kaaaaay, I think it’s time to get started!”

 

* * *

 

Family day was wonderful. Everyone took family pictures, played games, and mingled. The kids even taught their parents a lesson on ‘colors’. Troy and Abed behaved themselves and helped Annie keep everyone on track. She thought the day was an absolute success.

Everyone was heading home when Annie started cleaning up. She was wearing a smile on her face when Jeff walked up behind her. He tapped her on the shoulder, causing her to jump in surprise.

He stifled a laugh behind a lopsided grin.

She scoffed at his laughter, “I didn’t hear you walk up behind me, it’s like you have rabbits on your feet!”

That made him laugh even more, “Rabbits? I don’t think that would be humane…I should tell Britta what you said.”

Now she was laughing along with him. “No! We would never hear the end of it.”

They held each other’s gaze once again before Jeff spoke again, “I, uh, just wanted to tell you that today was really great. Matthew was really excited for me to spend the day here. And he seems really taken with your roommates,” he turned to look at Abed and Troy acting out some elaborate action scene with his son. “He’s usually really shy with strangers but he really likes them.”

Annie glanced over at them, “Yeah, they’re loveable goofballs.” She looked back to Jeff and smiled, “but I’m glad you enjoyed yourself. It was cute.”

Jeff was clearly surprised by her use of the word ‘cute,’ but being the guy he is, it definitely stroked his ego.

When Annie realized what she let slip, she tried to recover, “Everyone was cute…with their kids.”

“Yeah…So do you need any help?” Jeff looked up at the banner that Annie was attempting to take down before he snuck up behind her.

“Oh, yeah! That would be great actually. I was having trouble reaching this thing.”

Jeff laughed and reached up to tear away the tape holding the banner to the wall. “Yeah I could see that. It must be difficult getting through life at your tiny size.”

“I’m not tiny! You’re just abnormally tall! I could have gotten it down… I just needed a stool. Or a chair,” she flipped her hair over her shoulder to punctuate her statement.

Jeff handed her the detached banner, “Well then Ms. Edison, I guess I made your life a little bit easier.”

She rolled her eyes at his smug smile, “I don’t know what you mean, Mr. Winger.” She sent him a playful smile over her shoulder when she turned to walk away.

Okay… Maybe this was a little more than semi-flirtatious.

**Notes for the Chapter:**

> I forgot to mention in the first chapter notes that I decided to name Jeff's son Matthew rather than Sebastian because I feel like Sebastian would be the name of Jeff AND Annie's son (if they were to ever have one together in this universe...)


	3. It's only been a year

**Summary for the Chapter:**

> Jeff has a conversation with Shirley.

**Notes for the Chapter:**

> This chapter takes place a few weeks after Family Day.

Jeff was feeling good. He was relieved to find out his son was actually enjoying preschool. He was making friends, learning a lot, and he seemed to be all-around happier. Maybe this was the change he needed. Matthew was no longer sitting at his grandmother’s waiting for Jeff to get home from work, he wasn’t begging to stay at Shirley’s instead of going to school. He spent less time thinking about his absent mother and more about what Ms. Edison was teaching him in class. He was really enjoying himself and the new development.

Jeff was helping Shirley clean up after their annual bi-weekly dinner when she brought up the change in his mood.

“What’s gotten you all smiley today, Jeffrey?” Shirley eyed him suspiciously as she removed the dirty plates off of her dining room table.

Jeff let out a laugh as he began to load the dishwasher, “What do you mean?”

“You know what I mean. You haven’t said anything remotely sarcastic all evening and you didn’t even crack wise when I invited Matthew to Elijah and Jordan’s Youth Group!” She joined him at the dishwasher.

“I’ve been plenty sarcastic, Shirley. And just because I didn’t comment on the youth group thing doesn’t mean I wasn’t thinking it…” He grinned at her.

“Mhmmm.” Shirley eyed him again. “Something’s up with you.”

Jeff shook his head. Leave it to Shirley to notice even the smallest details. He could always count on her to call him out on his bullshit too. He was really grateful to have her in his life. She’d helped him get through his split with Kristen ( _I know a couple of jukeboxes that can take care of her, Jeffrey…_ ) And being a single dad was insanely difficult, but Shirley was there whenever he needed her; whether it was to baby-sit, offer advice, or just support him whenever he needed the extra motivation.

Jeff sighed, “I don’t know, Shirley. I guess things are just going well right now. Matthew is loving school and making friends. I was kinda worried he’d take after me and hate it…but Annie really makes the whole experience fun for him.”

This got Shirley to look up at him, “Annie?” She was using her sweet, innocent voice to get him to elaborate.

Jeff turned back to loading the dishwasher to avoid her questioning gaze, “Oh, uh yeah. Ms. Edison. Matthew’s teacher.”

Shirley raised her eyebrow, “You’re on a first name basis with Matthew’s teacher?”

“Yeah. So what?”

“So what?! I don’t know about you, Jeffrey, but it sounds like this Ms. Edison is a little more than Matthew’s teacher!”

Jeff crossed his arms over his chest and faced his friend, “What’s that supposed to mean?”

“You know exactly what I mean. C’mon Jeffrey, you can’t expect me to believe that your good mood is only because Matthew is enjoying himself at school. These past few months have been really different. I haven’t seen you or Matthew this happy in a long time,” Shirley mirrored his position.

“I’ve been happy!”

She shook her head, “Not like this.”

Jeff shrugged, “I don’t know what to say, Shirley. Things have just felt a little easier lately.”

She seemed to have accepted his answer, but it was only a moment before she asked, “Does this have to do with a woman named Annie?”

He sighed and avoided her gaze.

“Do you like her, Jeffrey?” Shirley’s voice was soft.

Jeff finally gave in and rolled his eyes, “Yes, Shirley. I like her. Happy?”

She clapped her hands and cooed, “Aw, Jeffrey! I am! What’s she like?”

He was reluctant to answer, but once he did, he couldn’t seem to stop. “I don’t know…She’s really beautiful. Seriously beautiful. She has bright blue eyes, brown hair. She wears bright colors and is all around positive. She is insanely adorable but extremely stubborn all at once. And she’s genuinely funny. She’s just…different.”

Shirley was elated, “She sounds lovely.”

He couldn’t take anymore of her ‘knowing’ eyes so he went to go make a few cups of coffee for the two of them, “Yeah well, don’t get your hopes up…”

Shirley’s face turned as serious as ever, “And why the hell not?”

Jeff was surprised at her change of tone, “Because…She’s Matthew’s teacher. I can’t ask her out…That would complicate everything. Plus, isn’t there a rule against it or something? ‘The Don’t-Date-Your-Kid’s-Teacher-Unless-You-Want-to Ruin-Their-Social-Life Rule?”

“Don’t be ridiculous! He’s only four years old. That won’t affect him in the slightest. And she’s only going to be his teacher for a few more months!”

“I don’t know, Shirley. I just don’t see this situation ending well. And… It’s only been a year since Kristen left…I have Matthew to think about,” he looked over at his son playing with Elijah and Jordan in Shirley’s living room.

“Jeffrey. Look at me.” Shirley’s serious tone was back.

He looked at her, waiting for some sort of lecture.

“Now you know that I was never a fan of Kristen. And what she did to you and Matthew is unforgivable.”

Jeff nodded his head and glanced at the floor, feeling a twinge of hurt in his chest. What she did _was_ unforgiveable.

“But I haven’t seen you feel this way in a long time.”

“Shirley, it’s only been a year‒”

“No, Jeff. That’s not what I’m talking about. You can deny it all you want, but I know you weren’t happy even when she was around. You and Kristen had your issues, but even during your best times, you were never truly happy. That woman was crazy to leave you two, but let’s be honest. There wasn’t any love there.” She reached over to grab his hand, “And you deserve to be loved, Jeffrey. And so does Matthew.”

Jeff finally looked up at his friend and gave her a genuine smile. “Thanks, Shirley.”

 

* * *

 

The whole car ride home from Shirley’s, Jeff couldn’t stop thinking about what she said about being happy. He was in a good place, maybe he _should_ make a move with Annie…He wasn’t even sure if she shared the same feelings… but the flirting was definitely going both ways.

Wasn’t it more than flirting though? Sure, they had their morning banter, but it had been growing into something more. Jeff couldn’t even pinpoint the moment when he realized seeing Annie was the better part of his day (apart from spending time with his son). It just sort of happened.

Jeff snapped out of his thoughts when Matthew called from his car seat.

“Daddy?”

He looked back at his son through the review mirror, “Yeah, buddy?”

“Auntie Shirley lives with Uncle Andre and Elijah and Jordan. Why doesn’t mommy live with us?

Jeff’s heart constricted in his chest. He knew this conversation was coming. He’d tried to explain it when Kristen left last January, but he was too young to really understand. But he knew that now was the time to try again, “Well, uh, mommy and I aren’t…together like Auntie Shirley and Uncle Andre.”

“Why not?” Matthew was staring out the window, watching the passing street lamps.

“Well, your mom and I wanted different things. And we were very unhappy.” Matthew was silent, so Jeff continued hesitantly, “Do you miss her?”

“Sometimes.” He paused before continuing, “But I want you to be happy.”

Jeff’s breath caught. His son was the greatest gift he was ever given. He couldn’t believe how lucky he was. “I want you to be happy too, buddy,” Jeff looked back at his son.

As much as he didn’t truly believe it, he knew it was what his son needed to hear, “Matthew, I know it’s hard to understand, but your mother just needed to be on her own for a while, okay?”

“Okay.”

Maybe Matthew wouldn’t understand yet, but he would someday. Until then, he had Jeff. And Shirley and his grandmother. He had people who loved him no matter what. But maybe it was time to make room for someone else.

Maybe it was something that they both needed.

 

* * *

 

It had been a few days since he and Shirley had their talk and Jeff had been thinking about it a lot. He had been happier. And he truly did like Annie. Their daily five-minute conversations weren’t enough anymore. He wanted to spend hours with her. He wanted to spend time with her without being surrounded by twenty screaming children. He wanted to brush her hair over her shoulder. He wanted to make her blush. He wanted so badly to kiss her.

So when he went to pick up Matthew on Friday afternoon, he was going to do something about it.

Jeff walked into the classroom and scanned the room until he spotted Annie, putting a few books onto one of the many bookshelves in the room. He saw Matthew playing a game with Emily and a few friends, so he figured this was his best opportunity.

He walked up and leaned against the frame of the shelf, “Afternoon, Ms. Edison.”

She looked up from her crouched position on the floor and shot him a wide grin, “Hello, Jeff.”

“Need any help?”

She climbed to her feet and brushed her hands along her skirt, “No thanks, all done. How was work today?”

“It was alright,” he grinned. “Good to be back here though.”

Annie’s cheeks grew pink. “I’m sure the best part of your day is seeing your son.”

“It most definitely is. But this place has other perks too,” Jeff held her gaze.

Still blushing, Annie looked down and brushed hair behind her ear.

When she didn’t speak up, he knew it was the moment.

“You know, much as I love the smell of glue sticks and crayons....”

Annie laughed and rolled her eyes.

“I’d really love to spend time with you someplace else.”

Annie’s eyes grew wide, surprised that Jeff actually made a move. But in the next moment, he could see her entire expression relax and a smile creep across her face, “And where might that be?”

After seeing her smile, Jeff visibly relaxed as well, “I don’t know yet, but I was thinking…Dinner?”

She was smiling at and nodding her head, “I would love that.”

Jeff was beaming, “Great. Does tomorrow night work?”

Annie was surprised at how soon these plans were falling into place, “Oh! Yeah, that works for me.”

“Alright then. I’ll call you?”

“Oh, right! I’ll give you my number. Umm…” She was frantically looking around for paper and a pen. She spotted a notepad on her desk and quickly wrote her phone number.

When she handed it to Jeff, he laughed at the ‘You’re a Smart Cookie’ stationary. “Thanks. So I’ll call you later?”

“That would be great.”

Jeff grinned at her one last time before walking over to Matthew.

_Oh my God, I have a date with Annie Edison._


	4. You should stay

**Summary for the Chapter:**

> Jeff and Annie have dinner.

Annie was nervous. She was undoubtedly excited, but she couldn’t help but feel like her insides were twisting frantically. Jeff had called her the previous night to make official plans for their date. They decided to keep it light and casual, so rather than going to some swanky, expensive restaurant, they were going to have dinner at his place, just the two of them.

She was checking her outfit for the sixth time that night when Abed walked to the entrance of her room, “Hey, Annie.”

She was startled but quickly regained her composure, “Abed! Hi.” She went back to smoothing out imaginary wrinkles in her dress.

He cocked his head to the side, “Are you nervous?”

“Is it that obvious?”

“Why are you nervous?”

Annie was twisting her hands before her, “I don’t know. I just…Maybe we shouldn’t be doing this. He’s the father of one of my students. This can’t be a good idea, could it?” She looked at Abed hopefully.

Abed walked further into the room. “Annie, you really like Jeff, don’t you?”

“Well…yeah.”

“And he likes you?”

“I…I think so.”

“Then you have nothing to worry about,” he said simply. “You guys are in this together, it will all work out.”

Annie smiled gratefully at her friend, “Thanks, Abed.”

“I really like Jeff. I think he’s good for your character arc.”

She ‘awwwed’ and ran to hug her friend.

 

* * *

 

Annie arrived at his apartment precisely at eight o’clock. She spent a few moments in silence before knocking on the door. _C’mon, Edison. Just do it._

When she finally did, it was only a quick moment before Jeff opened his door. He had a wide grin on his face and he looked absolutely charming. Instead of his typical suit or casual button down, he was wearing a blue sweater with dark jeans. His hair was perfectly disheveled and his stubble was as handsome as ever.

“Good evening, Ms. Edison.”

She rolled her eyes and smiled, “Jeff.”

He took in her casual navy dress, which was different from her usual skirt and colorful cardigan. She let her hair fall naturally rather than pin it to the side, and he definitely took note. When he realized he was still standing in the doorframe, he stepped to the side to invite her in the apartment, “Come on in.”

They were both standing in the entry way smiling at each other when the oven timer loudly sounded through the apartment.

“Oh, uh, I should get that, I’ll be right back!”

Annie smiled and nodded and had a look around the apartment. It was a good size, perfect enough for two or three people. Matthew’s toys were lying here and there throughout the room, by the TV, near Jeff’s desk. His laptop was closed but his briefcase was left open, he was most likely completing some work earlier. There were picture frames sitting on top of flat surfaces, some filled with the father and son together, others with a woman that looked to be Jeff’s mother. Some were of another family, most likely close friends. Annie smiled at the thought of Jeff printing photos and placing them around the apartment. He had such a ‘cool guy’ façade but he was a total sweetheart underneath it all.

She was looking at a photo of Jeff and Matthew that was taken on Family Day when he returned from the kitchen. “Hey,” he smiled, hands in his pockets.

“Hi!” She put the frame down and walked towards him, “I love all of your photos. They’re all so adorable.”

Jeff laughed bashfully, “Thanks. My mom bought me a bunch of frames so I figured I’d use them.” He paused a moment before remembering to offer her a drink, “Oh, hey, did you want a glass of wine? Or scotch, I have scotch,” he gestured towards the kitchen.

“Wine would be nice!”

“Right this way, then.”

She followed him into the kitchen and she was greeted by a delicious aroma of home cooked food, “It smells amazing, Jeff!”

“Oh, thanks! I’m not just a handsome lawyer, I’m also a handsome cook too,” he began pouring the bottle of red wine that was sitting on the counter.

“So modest,” Annie laughed.

Jeff handed her the glass of wine and took a sip from his own, “You look really great by the way.”

Annie blushed over the rim of her glass, “Thank you.” She continued to smile, “so do you.”

He shot her a lopsided grin as she walked over to the refrigerator. She noticed that it was covered with Matthew’s drawings. There was barely any stainless-steel peeking through, “So many drawings.”

 Jeff chuckled, “That’s your doing, you know.”

“What? How is this my doing?” She was surprised yet amused.

“Because, he makes at least four of those at school every day and then he spends twenty minutes deciding which ones I should hang up on there,” he nodded towards the refrigerator.

“Well drawing is actually a great way for children to practice their motor skills and sharpen their minds. Maybe you should be thanking me,” she playfully lifted her shoulders.

He laughed, “Hey, I’m not saying it’s a bad thing. I love these things. I have a bunch more hanging in my office at work.”

Annie’s eyes grew wide, “That is adorable! Where is Matthew tonight, anyway?”

“He’s at my friend Shirley’s, actually. She has two boys of her own, so she offers to babysit a lot. He’s actually staying the night, so we’ll have the place to ourselves.”

Annie choked a bit on her wine at Jeff’s words.

His eyes bulged when he realized what he said, “I don’t mean we have to…I- I mean I’m not expecting…” He was rambling, trying to find the right words. He took a breath and finally found them, “I just meant that we don’t have to worry about any interruptions.”

She giggled at his flustered state and nodded her head, “I understand.” She tried to help him out by switching topics, “How about we eat this delicious dinner? I don’t think I can wait anymore.”

Jeff shook his head and laughed, “Yes, why don’t we?”

 

* * *

 

The dinner was wonderful. After commenting on the food, they talked about work, interests, other school parents (because they both really can’t stand Jonathan’s dad). It was nice and easy and all around enjoyable. After they had finished their meal they went to relax on Jeff’s couch, refilled wine glasses in hand. The meal was delicious and Annie was thoroughly impressed, “Jeff, dinner was amazing. I’m stuffed.”

Jeff laughed and shook his head, “Thanks. It was nothing. Just a few skills that I picked up from Shirley.”

Annie tilted her head, “You’re really close with your friend Shirley, aren’t you?” She smiled at him.

He took a sip from his wine and then placed it on the coffee table, “Yeah I am. She’s been a great friend.” He paused before he continued, “She, uh. She really helped me out with Matthew this past year. I don’t know what I would have done without her.” He smiled crookedly at her.

“That’s really sweet.” Annie was thoughtful for a moment. She wasn’t sure if she should ask, but…it was kind of looming in air, it had to happen sooner or later right? “What happened to Matthew’s mom?” she looked at him curiously.

Jeff nodded and sighed, “Well….” He grabbed his wine glass and drained what was left before he put it back down. “Uh…about a year ago Kristen left us. Things weren’t…working out for us anymore so she decided to leave.”

Annie reached and put a hand on Jeff’s arm that was draped along the top of the couch, “Jeff. I’m so sorry.”

He smiled and waved off her concern, “It’s alright. We’re doing fine.”

“Yeah, you are. But…I know divorce can be tough. My parents went through the same thing when I was a kid.”

“Kristen and I actually weren’t married.”

Annie was surprised, “Oh!” She moved her hand that was still resting on his arm.

Jeff chuckled at her surprised reaction, “We were engaged though.”

“Ah…It still must have been hard. Especially because of Matthew…” She looked at him sympathetically.

“We were dating for a few months and then she found out she was pregnant,” he began.

Annie gasped softly.

“Yeahhhh. And I wanted to do the honorable thing, so I asked her to marry me,” he said it matter-of-factly. “Things were okay. They weren’t great. We both kind of knew that Matthew was the real reason why we were staying together. But she told me she wanted this, she wanted a family. And she wanted it with me. So I really tried. I gave her the house, the partnership…” He trailed off and thought a moment before continuing. “But I think she was fooling herself because after three years she packed up and left.”

Annie shook her head, “Where is she now?”

He laughed and looked at her, “I have no idea. She calls every few weeks to talk to Matthew but that’s it. I don’t even want to know, if I’m being honest.”

“How is Matthew taking it?” She asked him.

“He says he’s okay, but I know he’s really confused about the whole thing.” He was quiet for a long moment, clearly hesitant to say his next sentence, “I understand though, because the same thing happened to me with my dad.”

Annie’s heart broke, “Your dad left you and your mom?”

Jeff cleared his throat uncomfortably, “Yeah, he did. I wasn’t as young as Matthew though, six or seven. So I know how he’s feeling. It just kills me because I can’t believe he has to go through it too. I wouldn’t wish it on anybody,” he shook his head.

Annie understood. Granted, it wasn’t the same situation but she too was abandoned by her parents. She got hooked on pills, sought help, and then they cut her off. She knew what it was like to be unwanted.

“I think…” Jeff swallowed thickly, “I think that’s why I tried so hard with Kristen. I didn’t want to be my dad. I wanted to prove that I could be a good husband and a good father. I just wanted to be everything he wasn’t.”

Annie was taken aback by how open Jeff was being. She knew it was significant that he was revealing this to her, so she put down her wine and moved closer to him on the couch. She wasn’t sure what to say because she really didn’t know what his dad was like, but she knew Jeff was nothing like him. She could tell he felt open and vulnerable for dumping his broken past on her. She didn’t want him to feel alone.

“When I was seventeen I got hooked on pills and ruined my future,” she was looking right into his eyes. He wasn’t alone, she was right there with him.

He was caught off-guard by her confession, “What?” He looked at her curiously.

She didn’t skip a beat. “I went to rehab to get help and then my parents cut me off. I haven’t spoken to them in over eight years.” She saw his expression change from vulnerable and surprised to compassion and understanding.

She felt closer to him. He told her about his dark history and she told him of her shameful past. There _was_ energy running between them and she was drawn to him, like they were both magnets. Two empty beings that needed to feel whole again.

There wasn’t much time to think because in the next moment, they were surging towards each other, lips crashing together furiously. Annie held his face in her hands and leaned forward until she was practically straddling him. One of Jeff’s hands gripped her leg while the other made its way up her back, holding her in place.

His body was warm against hers but his lips felt even better. All of the flirting and tension built up over the past months came rushing to the forefront. But it was more than that. They opened up to one another, trusted each other with their fears and secrets. Something shifted, but in the best way possible.

They pulled a part for a breath but neither of them could speak. They were both filled with lust and longing and compassion for one another.

After Jeff controlled his breathing, he looked from her lips to her eyes, “Annie, I had no idea.”

“We all have things were ashamed and afraid of Jeff. You’re not alone,” she smiled sweetly at his vulnerable expression and kissed it right off of his face. He eagerly accepted her lips and held her closer.

They fervently made out for a few long moments until Annie’s hands made their way under his sweater. She began to pull it over his torso but Jeff stopped her, “Annie, we don’t have to do this tonight.”

She was inches from his face, looking deep into his eyes with the hem of his sweater bunched in her hands, “I know. I want to.” She leaned into to capture his lips once more but then quickly retreated, “Wait, do you want to?”

Jeff huffed out a laugh, “Yes. I really do.”

“Good,” she pulled him in for a deep, slow kiss.

Jeff’s hands found the zipper of her dress and he began to tug lightly. He pulled it down to the small of her back and the fabric fell loose around her shoulders. She felt his hands move to grip her thighs and he carefully lifted them both from the couch. Jeff found his footing while Annie’s legs were wrapped around his waist.

She gripped his shoulders and let him carry her blindly to his bedroom, kissing all the way there. When they reached the foot of his bed, he gently released her and she slowly slid down his body until her feet touched the floor. They were staring at one another when Annie let the dress drop to the floor, leaving her in her black bra and panties.

Once his gaze became too much, she looked bashfully at the fabric on the floor until she felt his thumb and forefinger grip her chin. She met his eyes once more and he was smiling.

“You’re really beautiful.”

She thanked him by reaching onto her toes and soundly kissing him on the lips. “You’re not so bad yourself,” she slipped her hands under his sweater and felt the contour of his muscles.

Jeff grinned at her and pulled the shirt over his head and threw it somewhere across the room. She was ogling his perfect abs and broad shoulders when he pulled her in for another kiss. Before she knew it, they were shuffling onto the bed. Annie made her way onto her back, her hair flaring out on to the pillows. The room was dim and soon the only thing she could see was Jeff looming over her.

 

* * *

 

It was a while later, and they were under the sheets, heads resting on the pillows facing each other. They had been silently watching one another for a few long moments, reflecting on the previous events of the night. Annie was overcome with an emotion that she couldn’t exactly explain. She’d never felt so close to someone before. Sure, she’d been in relationships before, but this was the first time that she felt understood.

Jeff was the first to speak, “That was…”

“Amazing,” she finished for him.

He chuckled and took hold of one of her hands.

Annie looked at their entwined hands and smiled. “Jeff,” she whispered, “I don’t really tell people about my addiction, but you were the first person who didn’t immediately look at me differently.” She ran her thumb over his. “Thank you.”

He smiled and her and then took in a deep breath. “I don’t ever talk about my father. But you made it…easier to.”

Hearing him say that made her heart swell ten sizes. She leaned forward and placed a soft kiss to his lips. She wished she could stay in that moment forever, tangled in the warm sheets with him. She felt safe, like she always belonged there. But as much as she hated the thought of leaving, it was after midnight and she knew it was probably time to go.

They were inches apart, marveling in their moment when she finally brought herself to speak again, “It’s late…I should probably go.” The last part came out in a whisper.

“You should stay,” he eyes were searching hers.

She smiled at his offer, “You want me to stay?”

“Yeah, I mean, like you said. It’s late,” his hand gripped hers even tighter, “And I want you to.”

She felt butterflies consume her entire body, “Okay. Then I’ll stay.”

They didn’t say much else and they soon drifted to sleep.


	5. He wants me to be happy

**Summary for the Chapter:**

> Jeff has a few conversations.

**Notes for the Chapter:**

> I've decided that this will be the last "normal" chapter of 'Just the Way I'm Supposed to Be.' Chapter 6 is going to be an Epilogue. I really hope you've been enjoying this fic, I appreciate all of the kind words that I've received!

It was early in the morning, probably around seven-thirty, and Jeff was waking up from a fantastic sleep. He felt warm and content, like he never wanted to leave his bed. It took him a few moments to regain full consciousness, but once he did, he realized his arms were wrapped around a sleeping Annie Edison. Her back was pressed against his chest and his face was pressed against her bare shoulder.

He found himself getting lost in the scent of her fruity shampoo for what must have been the hundredth time in the past twelve hours. He couldn’t help himself, she was just irresistible. And she was warm. And so unbelievably comfortable. He wanted her in his bed forever.

Jeff tried to think of the last time he spent the night with a woman other than Kristen. This was all new to him because Jeff Winger did not have sleepovers with women. They did the deed and then parted ways. That’s what he had always preferred, it was what he knew.

But that changed with Kristen. A few accidental sleepovers turned into a consistent routine and before he knew it, they were in a relationship. Jeff sort of just adapted to the whole situation. But after a few months they slipped up and found out she was pregnant. It was never in his plans but life happens…And even after all of the crap Kristen put him through, he still wouldn’t change it because Matthew has given him everything.

But when she left, he told himself he would never put himself or his son through that again. The world was a crappy place with crappy people. They had all of the support system that they needed… But then he met Annie. Things were different, _she_ was different. He didn’t fall into her trap, the two just collided. He couldn’t control it. And he didn’t want to.

That’s why while he was lying there wrapped around Annie, he knew it all made sense. They didn’t spend the night together accidentally, he asked her to stay. For the first time in his life, Jeff Winger asked a woman to stay over because he couldn’t imagine her leaving.

After a few moments of being lost in his thoughts, he felt Annie stir awake. He thought about pretending to be asleep so she would stay put, but he decided against it. _Get a grip, man_. Instead he loosened his hold and kissed her shoulder, “Good morning.”

She turned in his arms so she was facing him, she had a bright smile on her face. “Morning,” she giggled. “What time is it?”

Jeff looked over at the clock on his nightstand, “Just past seven-thirty.”

Annie let out a small groan, “I don’t want to leave this bed, these sheets are luxurious.” When Jeff chuckled, she wrapped an arm around his torso, “but the company is pretty good too.”

“Glad I made the list,” he leaned forward and pecked her softly on the lips.

 

* * *

 

 

Jeff had the chance to once again show off his cooking skills when he and Annie retreated to the kitchen for some breakfast. He made her one of his signature egg white omelets and she even let him brag about it. It was after they were both fully dressed that they decided to have _the_ conversation. It was something that they both knew was coming. They avoided it long enough.

Jeff was sitting on the arm of the couch while Annie was gathering her things to head home. “So,” she said when she went to stand in front of him. “What happens now?” Her voice matched her expression, questioning and hopeful all at once.

“Well,” Jeff gripped her hips and tugged her closer, “I _really_ like you.”

Annie smiled and ran her thumb along his stubble, “I really like you too.”

“And I think we should do this again,” his arms made their way around her waist, bringing her even closer.

“I’m Matthew’s teacher…” she sighed.

“Which is why…” Jeff nuzzled his nose along her jaw, “I think we should do this again, but we’ll keep it to ourselves. For now,” he looked into her eyes. “You’re only going to be his teacher for a few more months… Until then, we can keep it professional at school and very _unprofessional_ everywhere else,” he smirked at her.

“Jeff!” She laughed and swatted his chest. “Are you sure this is a good idea? What will Matthew think?”

 _He wants me to be happy_. “I’ll talk to him. But trust me, he loves going to school every day _because_ of you. I think he’ll be excited that you’ll be around a lot more.”

Annie looked at the floor and blushed, still not completely convinced.

Jeff gripped her chin and tilted her face to his, “I’ll talk to him, I promise. But believe me, this will be good for the both of us. And I would never do something that would hurt him, okay?”

She smiled, “Okay.”

Jeff walked Annie to the door and they said their goodbyes. He promised to call her later that night and they shared a sweet kiss.

“Professional at school tomorrow?” She quirked an eyebrow at him.

“I promise! The screaming children and animal cracker smell really kill the mood anyway.”

She scoffed and turned to leave. “Bye, Jeff,” she looked over her shoulder.

“Bye, Annie,” he watched her walk to the elevator. Once she was inside, he retreated back into his apartment and flopped onto his couch and tried to make sense of everything he was feeling. He wasn’t completely sure, but it was a good feeling.

 

* * *

 

Later that Sunday afternoon, Jeff headed to Shirley’s to pick up his son. It was the first time in a while that Matthew had spent the night away, so Jeff was eager to see him. He knew that when he arrived at his friend’s house, she would bombard him with questions and demand details of his date. As much as he was dreading that, he was dreading the car ride home when he planned to talk to Matthew about Annie. Jeff knew that Matthew would be okay with it, he just hoped that he understood that some things would be changing.  

“Hey, Shirley,” Jeff smiled at her from outside the front door.

“Jeffrey! Come in, come in,” She was already walking towards the kitchen so Jeff followed suit. “Matthew was a delight as always. That boy is the sweetest child I’ve ever met…I wonder where he gets it from.”

“Hey! What’s that supposed to mean?” Jeff crossed his arms and leaned against the counter.

She swatted the air and chuckled, “I’m just kidding, I know you can be sweet when you want to be.” She was already getting two coffee mugs out from the cabinet, “But how was last night? You better tell me everything!”

Jeff sighed but couldn’t hide his smirk, “It went really well.”

“And…” She was clasping her hands in front of her.

“And…We’re gonna do it again.”

“Oh, that’s nice!” Shirley was pleased. “Tell me how it went, what was she like? What did you do? Did you cook for her? What did you talk about?”

“Geez, Shirley. Take a breath, why don’t you.”

His sarcasm didn’t faze her, she just continued to smile with excitement, “Does she make you happy, Jeffrey?”

He was reluctant to answer but he knew he had to anyway, “Yes, Shirley. She makes me happy.” _I’ve never felt so close to someone. She’s easy to talk to. She understands me._ Jeff thought about all of those things, but he wasn’t about to tell Shirley that. She’d probably burst with excitement.

“Good. Now I can stop pestering the poor single women at church about the ‘handsome single dad who needs help finding the Lord’s word,’” she pat him on the shoulder and went to pour the coffee.

Jeff looked at her ridiculously, “You’ve been doing _what_ now?”

Shirley didn’t have time to respond because in that same moment Matthew ran into the kitchen excited to see his father, “Hi Dad!”

Jeff’s face lit up and he reached to lift his son into his arms, “Hey, Matthew! Did you miss me?”

“Mhm,” he was smiling ear to ear.

“Good because I missed you,” he kissed his head. “Did you have a good time with Auntie Shirley?”

“We made brownies,” Matthew proudly stated.

“You did? Did you save me any?”

Matthew giggled, “Daddy, you don’t eat carbs!”

“I’ll eat them if _you_ make them,” he smiled at his son. “Alright, go get your things so we can give Auntie Shirley a break from all of this Winger charm.” He placed Matthew back on his feet and watched him run to the living room.

“Why on earth are you teaching that boy about carbs? He’s four years old!”

Jeff laughed, “It wasn’t intentional! He still eats them, don’t worry.”

“Mhmm.” Shirley looked at him suspiciously.

 

* * *

 

A little while later, Jeff and Matthew were headed home. Jeff thanked Shirley once again for watching Matthew and she responded by giving him a brownie and a knowing glance. “I expect to meet her sometime soon, Jeffrey!” She called out to him as he walked to his car.

“Bye, Shirley!” Jeff called out without looking back.

Once Matthew was strapped in, they were off. Jeff was waiting for the right moment to bring up Annie, but he couldn’t find the right words. _Just do it, Winger_.

“So, Matthew,” Jeff was looking at his son through the review mirror. “You’ve been enjoying school, right?”

“Yeah!” He was shuffling through a few drawings he made at Shirley’s.

“And you like Ms. Edison?”

“Yes.”

Jeff took in a breath, “Well, uh, Daddy likes her too…”

Matthew giggled which caused Jeff to look back at him with confusion. “Do you like her a lot, daddy?”

 _Maybe he does understand…_ “Yes, I like her a lot…”

This caused Matthew to laugh even more, finding his dad’s love life to be extremely entertaining. Jeff looked back at his son once more and began to laugh himself. He had no idea what was so funny but seeing Matthew laugh was contagious.

“What are you laughing at?” Jeff chuckled.

“You like Ms. Edison!” Matthew sing-songed.

 _My son is turning into Shirley._ He shook his head and smiled, “And that’s okay with you?”

“Yeah! I like her a lot. And I like her friends too. Troy loves Spider-man just like me and Abed told me about Inspector Spacetime! Can we watch that, Dad? Maybe they can come over and we can watch it together,” Matthew was talking excitedly from his car seat.

As Jeff listened to his son, he couldn’t help but feel a sense of relief wash over him. He already had a good feeling about it, but actually getting Matthew’s blessing was so important. If he could make his son happy, he knew he was doing this right.

Deep down, Jeff knew he would never be like his father. He cared deeply for his friends, loved his mother, worked hard at the things he loved, and he actually found someone he could open his heart to, but most importantly, he would anything for his son.

 

* * *

 

Jeff and Matthew spent the rest of the day together, watching TV and playing an array of different games. At some point in the evening, Jeff explained to his son that although he and Ms. Edison liked each other very much, they were going to keep it between the two of them for a while, but once school was over Annie would be around a lot more.

Matthew seemed to understand, but he was just glad his dad was happy. It’s all that really mattered.

So when Jeff went to drop Matthew off at school the following Monday morning, everything went on as usual. Matthew greeted his teacher with a smile and ran off to play with his friends. Jeff spotted Annie across the room and they shared a warm smile.

Annie walked over to Jeff, she was wearing the yellow sweater that she had on the first day they had met. She saddled up next to him, until they were shoulder to shoulder. They looked on as Matthew and Emily engaged in some sort of clapping game.

“Morning, Ms. Edison,” Jeff glanced at her and smirked.

“Hello, Mr. Winger,” Annie looked up at him with a wide grin.

It all seemed so normal, just like every other interaction they’ve had each morning for the past five and a half months. But it wasn’t. Now there was something between them, something that was honest and real and exciting. It was something that felt new but familiar all at once, like they were waiting for everything to fall in place.

And Jeff was finally in a good place. They all were.


	6. Epilogue

**Summary for the Chapter:**

> A look into Jeff and Annie's relationship over the next few years.

**Notes for the Chapter:**

> First and foremost, I would like to apologize for the great delay in posting this final chapter. I was tending to a few personal matters in the last couple of weeks, but I'm happy I was able to finish this up once and for all! It was rather difficult to tie up a story that had been moving at such a fast pace, so I hope his epilogue is satisfying. Thank you for sticking with me!

Seven months later

The summer had been going great. Annie and Jeff were still in a loving and exciting relationship and it had definitely blossomed over the last few months. Although they had been keeping it quiet while school was still in session, once June came around, Jeff and Annie no longer cared about the comments or questioning glances from other parents and teachers.

Annie had gotten closer to Matthew as well. As the calls from his estranged mother became less frequent, Annie became a more prominent figure in his life. At first she was worried that Matthew would reject her or push her away, but just as Jeff said, Matthew welcomed her into his life.

The summer had been filled with trips to the zoo, museums, walks in the park, and family get-togethers. Annie finally met Jeff’s good friend Shirley and they clicked right away. Matthew was spending more time with Troy and Abed who were slowly but surely bringing him out of his shell. It’s almost odd how this group of people came together, but somehow it makes perfect sense.

And before they knew it, August rolled around and they were celebrating Matthew’s fifth birthday. Matthew had taken a liking to astronomy so Jeff and Annie planned the party accordingly. Everyone was invited. Shirley baked the cake and brought Elijah, Jordan, and Andre. Abed and Troy thought of a number of games to play with the kids. Britta and Emily came early to help set up, and even Jeff’s mom came by to celebrate. Everyone had been getting to know one another over the summer, but now they were becoming an unstoppable group of no-longer-broken people.

A good time was had by all, but Annie’s favorite part of the day was after everyone went home and she and Jeff were wiped out on his couch, staring at the mess that lay around the place.

She was tucked into his side, his arm around her shoulders, and she was finally able to just relax. “I think everyone had a good time, don’t you?” She looked up at Jeff who was resting his eyes.

“Definitely. I also think Britta and Troy really hit it off…”

“What?!” Annie was gaping at him.

“Look, I’m just as shocked as you are,” Jeff was shaking his head.

Annie tilted her head, “Hmm. They would be cute together. And Britta deserves a nice guy for her and Emily. Troy really has the biggest heart… I hope it works out.”

Jeff was about to agree when a very tired Matthew shuffled into the room.

“Hey, buddy,” Jeff ruffled his son’s hair. “Did you have a good birthday?”

“Yeah! I can’t wait to play with my new Inspector Spacetime action figures!”

Jeff reached forward and picked up his son and placed him on his lap, “Yeah, maybe you can do that tomorrow. You should get some sleep. You had a busy day today.”

Matthew pouted but reluctantly agreed, “Okay…”

Annie giggled at the scene before her, happy she could share these moments with Jeff.

“Alright, say goodnight to Annie.”

Matthew crawled over Jeff’s lap and gave her a hug, “Night, Annie, thank you for today.”

“Goodnight, sweetie. I’m glad you had a good time,” she squeezed him tight.

When she let go he gave his dad a hug and said his goodnight.

It was when he started to walk towards his bedroom that he called back to both Jeff and Annie and said, “Love you guys!”

Annie’s heart grew in her chest at the sound of those words and she let out a small gasp. She looked over at Jeff with wide eyes and found him grinning ear to ear. Annie wasn’t sure if she could speak through the swell of emotion that was surging through her, but she found a way, “Love you too, Matthew.” Her hand was placed over her chest.

“Love you.” Jeff responded next.

Matthew walked straight to his room, like what he said was the simplest thing in the world. Maybe it was simple to him, because it was just how he felt, but to Annie, it meant everything.

Jeff gathered Annie close and placed a lingering kiss on her temple, allowing her to just marvel in the moment that their little family just shared.

* * *

 

Four Years Later

It had been only a year since they got married. They were in a solid relationship for three wonderful years but they finally decided to tie the knot and make things more official. When Jeff asked, she knew it was a significant moment after everything that had happened with Kristen. No matter how much time passed, abandonment would always painful. And Jeff experienced it twice.

So that’s why Annie was grateful that every morning she found him sleeping peacefully beside her. Sometimes his face was smooshed beneath the pillows, sometimes it was covered by his arms, and sometimes it was pressed against her shoulders. They were always mangled together in some capacity, but sometimes Matthew would be sandwiched between the two as they all slept soundly.

On this particular morning, however, Annie stretched out and rolled over in the sheets, finding her place tucked into Jeff’s side. He was still fast asleep so she happily sighed and closed her eyes. It was approaching midmorning but Annie decided to rest a bit more considering the fact that she was four months pregnant.

They were both lying peacefully until Matthew jumped on to the bed which awoke both Jeff and Annie.

“What the f‒” Jeff began as he regained his consciousness.

Annie quickly threw her hand over his mouth to prevent him from cursing in front of their son.

“Mmph.” He pried her hand from his mouth, “Hi, buddy.” Jeff ran a hand over his face.

Matthew crawled in between both Jeff and Annie and found a spot next to her baby bump.

Annie giggled at his fascination with his future sibling, “Do you think you’re going to have a baby sister or a brother?”

He smiled as he thought it over, “Hmmm…brother.”

“I think you’re going to have a baby sister,” Jeff said as he ran his hand over the bump himself.

“I think you’ll bet getting a brother too,” Annie said to Matthew.

Jeff began to get up from the bed and head for the bathroom, “Yeah, well we’ll see in nine months!”

“Brother,” she whispered and winked.

* * *

 

Seven Years Later

It turns out, Annie and Matthew were right. Five months after that morning, the Wingers welcomed a new baby boy into the world. Jeff didn’t get the chance to be disappointed at losing the bet because as soon as he laid his eyes on Sebastian, he felt nothing but love.

And seven years after they met, Jeff and Annie found themselves married with a twelve and three-year-old running around the house.

As usual, on this particular morning, Jeff was wrapped around Annie and she felt absolutely content. She was sound asleep until she heard whispering and dishes clanging at the entrance to bedroom.

“Shhhh, Sebastian. Mom and dad are still sleeping! We’ll just have to come back,” Matthew whispered at his young brother.

Annie appreciated the fact that the boys would let she and Jeff enjoy a little more time sleeping, but all peacefulness subsided when a loud clatter of silverware fell to the floor. Jeff and Annie both breathed in sharply and quickly shot up in bed.

“Oopsie,” Sebastian was standing near the doorway with a handful of forks and spoons on the floor by his feet. Next to him was Matthew carrying a tray holding toast, cereal, and juice, his eyes wide at the commotion made by his brother.

Jeff, not completely awake, ran a hand down his face, “Boys, what are you doing? It’s not even…” he looked at the clock on his bedside table, “…eight o’clock.”

“We wanted to make you breakfast for your anniversary!” Matthew was still holding onto a thread of excitement, though their surprise was slightly ruined by his younger brother.

Annie melted as the sight before her, “Awww! Oh my gosh, come here!” She held out her arms as Matthew put aside the tray and ran into his mom’s arms. She squeezed him tight and never stopped smiling.

Jeff, clearly taken aback by his sons’ sweet gesture, shook his head and smiled. He held out his arms to Sebastian, who was still standing in the pile of silverware, “Come here, bud.”

Sebastian happily ran over to his father and Jeff scooped the three-year-old up into his lap.

Annie leaned over to kiss her other son on the head as Matthew went to retrieve the tray. Not only was there breakfast, but also a handmade card and a single flower that was plucked from the flowerpot on the windowsill.

Jeff chuckled at the boys’ tactics and grinned at Annie as she got emotional over the card.

“I love you boys so much, thank you!” She gathered them close and pulled them in for a long embrace. Without her knowledge, Jeff snapped a picture on his phone before he ran his hand along his wife’s back.

“I couldn’t have asked for better sons to startle me awake early in the morning on a Saturday,” Jeff remarked sarcastically, but his smile was genuine. “Alright, what do you say we eat some of this breakfast. These carbs look delicious.”

So that was how Jeff and Annie spent their anniversary. With the two people they loved as much as they loved each other. Their family may have not begun in a traditional way, but they wouldn’t change a thing.

Jeff is thankful every day that he got to know Matthew’s preschool teacher. And Annie is thankful every day that she let him.

**Notes for the Chapter:**

> Well, that's it! For those of you who have been reading this fic, thank you for sticking with me. I really hope you enjoyed it! This was my first multi-chapter story and I enjoyed writing it. Thank you for all of the kind words and feedback over the the course of the chapters. I appreciated every word. Thank you, thank you!
> 
> Here is to many more AUs and the amazing Jeff x Annie fandom!


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